Born in Shropshire, Sommers came to the attention of Richard Fermor, a merchant of the Staple at Calais, who brought him to Greenwich in 1525 to present to the King. Impressed by his sense of humor, Henry promptly offered Sommers a place at court. He was soon in high favor with the King, whose generosity to him is attested by the accounts of the royal household.
Sommers remained in service to the King for the rest of Henry's life. In the King's later years, when he was troubled by a painful leg condition, it was said that only Sommers could lift his spirits.
The jester was also a man of integrity and discretion. Thomas Cromwell appreciated that Sommers sometimes drew the King's attention to extravagance and waste within the royal household by means of a joke.
Court jesters were permitted familiarities without regard for deference, and Sommers possessed a shrewd wit, which he exercised even on Cardinal Wolsey. He did occasionally overstep the boundaries, however. In 1535, the King threatened to kill Sommers with his own hand, after Sir Nicholas Carew dared him to call Queen Anne "a ribald" and the Princess Elizabeth "a bastard".
Robert Armin (writer of Foole upon Foole, 1600) tells how Sommers humiliated Thomas, the King's juggler. He interrupted one of Thomas's performances carrying milk and a bread roll. Will asked the King for a spoon; the King replied he had none. Thomas told him to use his hands. Will then sang:
This bit Harry I give to thee
and this next bit must serve for me,
Both which I'll eat apace.
This bit Madam unto you,
And this bit I my self eate now,
And the rest upon thy face.
He then threw the milk in his face and ran out. Thomas was never at court again.
Sommers used his influence to compensate an uncle who had been ruined by an enclosure of common land, although it took a very subtle appeal by Sommers to Henry.
In Thomas Wilson's Arte of Rhetorique (1553-60), Will is quoted telling the financially hard-up King, "You have so many Frauditors [Auditors], so many Conveighers [Surveyors], and so many Deceivers [Receivers] that they get all to themselves."
Sommers is believed to be portrayed in a painting of Henry VIII and family at the Palace of Whitehall. It was completed around 1544-45 by an unknown artist. Sommers also appears with Henry VIII in the Psalter of Henry VIII that was made for the King and is now in the British Library (MS Royal 2. A. XVI). A previously unknown picture in which Sommers appears was discovered in 2008 at Boughton House, Northamptonshire.
Today, entertainers sometimes perform as 'Will' in Renaissance-themed entertainments such as Renaissance faires.
After Henry's death, Sommers remained at court, eventually retiring during the reign of Elizabeth I.
Under Mary I, Will's role was mainly ceremonial, and as a sidekick to Mary's personal fool, Jane Foole. Will was reputed to be the only man who made Mary laugh, apart from John Heywood. Will's last public event was the coronation of Elizabeth I.
He was probably the William Sommers whose death is recorded in the parish of St. Leonards, Shoreditch, on 15 June 1560. A modern plaque in the church commemorates his burial there.
William Sommers made a number of appearances in sixteenth- and seventeenth-century drama and literature: for example, Thomas Nashe's Pleesant Comedie called Summers last Will and Testament (play first performed in 1592, published in 1600), Samuel Rowlands's Good Newes and Bad Newes (1622), and a popular account, A Pleasant Historie of the Life and Death of William Sommers (reprinted 1794). See also John Doran's History of Court Fools (1858).
Howard Goorney played Will Sommers in two episodes of the 1970 BBC miniseries The Six Wives of Henry VIII. David Bradley played Will Sommers in the fifth episode of the third season of the Showtime series The Tudors (2009). The real Sommers was younger than Henry VIII.
In Margaret George's 1986 fictional The Autobiography of Henry VIII, Will Somers protects the manuscript from Queen Mary, who would destroy it. "Somers" adds observations in his own hand that throw light on the old King's hypocrisies and failings.
In April 2016, Ottawa actor and playwright Pierre Brault premiered his solo show entitled Will Somers: Keeping Your Head, speculating on Sommer's life and the role of comedy has in speaking to power.
Will Somers is the main character in the historical novel The Last of Days by Paul C. Doherty. He is also the main character and narrator of the historical novel Fall of the House of Queens: Book One of The Shattered Rose Series (2017) by Shelly Talcott; in this fictional autobiographical account, while he is depicted as a hunchback (which historically he was not), he becomes a trusted confidente of not only Henry himself but also many of the important personages at court and all but one of Henry VIII's wives.